Process of making pungent compounds



Patented Aug. 5, 1924 UNITED STATES.

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To all whom may concern i Be it known that. we, DONALD .13. Beam NER and MARY L. SHEnRILmcitizensof "the United States, residing at Baltimore, Ma-ryland,-h'ave invented certain new and useful Improvements in Processes of JMaking Pungent Compounds, of which the following is a specification.

. This invention relates to a process of lo'making pungen't compounds and has more specific application to the preparation of capsaicin, which is the pungent principle of cayennepe-pper. 1 i

These pungent compounds have been synthetically made heretofore by. first preparing vanillyl amine came:

. on a h I Y and then condensing the latter with an acid chloride of 'the. eneral formula-(1H,:

COGI resulting in the formation of the compounds is not only cheap but is highly eificient and involves the use of readily pro curable materials.

In preparing the pungent compounds according ,to our invention, guai acol is condensed vwith a compound of'the general formula RGONHC-I-LX wherein R is an .alkyl radical containing from 6 to 11 carbon atoms and X represents a simple radical which combines with a hydrogen. atom of thearomatic roup of aiacol to form a substance" reag' among which may be mentioned the use of the Friedel-(lrafts synthesis in which case X represents a halo en in the general for-.

mula, and; a suitab e condensing agent is,

employed to bring'aboutsuch synthesis.

7 We prefer, however,'to carry outour process by em loying an oxymethyl acylamide,

where in t e above general formula X rep- 5 resents a hydroxyl group, OH, and bring.-

ing about a reaction of the oxymethyl Application flled May. 7,

ceno'yl-amide and. 50 e are dis'solvediin about" 650 cc. of ahsolute,

11y separa le from'the pun-- gent product. Several methods maybe employed for bringing about this reaction,.

PUNGENT comrounps'. 1923. Serial mi. 635,369. I

acylamide with guaiacol 'in 'the presence of a dehydrating agents The oxymethal acylamide is first prepared by the action of formaldehyde on the acylamidei-n the pres-- ence of an alkaline condensing agent.

; The general reactions'areas follows:

RGO'NHQH H O H, omooHQ:

A- specifie example of carrying out our process is as follows: About 100' grams of undecenoyl amide, G H CO'NH and 5.5 grams of barium hydroxide are'mix'ed with 145 grams of a 40% formaldehyde solution.

The temperature is raised to about 70 (3., v Q

it at which it is held for about 3 minutes and then allowed to'cool slowly. The oxymethyl H ,,OONH OH,QI-I, is r unde'cenoyl amide removed hy filtra ion;

Aboutgrams of-the oxymethalunde grams of guaiacol alcohol and 50 001 of concentrated H,,SO,,

are added while th mixture is being cooled.

The mass-isallowed tostand for about '5 then extracted with a suitable organic liquid, such as CHCL, and the (ll-1C1 solu-' tion is washed with dilute M 00, solution.

jThe-pungent. material is then recovered by;

distilling oft the GHCl Our invention comprises the-employment" of any aliphatic acylamide containing 7 to' 0r-6 days at room. temperature and then poured. on ice, The pungentmaterial is '12 carbon atoms which may be employed in lieu of undecenoyl amide and also other dehydrating agents, for example, ZnCh, may

be'used instead of the H 80 Also,gif-

sufficient dehydrating agent is employedordinary alcohol may be used instead of absolute alcohol; I 1

The ac lamide may treating t e corresponding ac d, for example undecylenic acid, with PCI, to form the acylamide'chloride, which is then treated- NH,OH solution and the undeoenoyl' with amide separated by filtration.

The present-invention s not limited e p d l e Y 3 the specific details set forth in the foregoing examples which should be "construed as illustrative and not byway of limitation and in view of which may beeifected flthereingwithout departing from the -'spirit and scope of this the numerous modifications invention, it is desired that only such limits tions be imposed as are indicated in the: ap pended claims. e a

We claim as our invention:

'1. In a process of making pungen pounds reacting guaiacol with a'compound of the formula RCONHCH X wherein R ispounds, condensing guaiacol with a compound of the formula RCONHCI-LX wherein- R is an alkyl radical containing fromQG to 11 carbon atoms and X represents a simple radical'which combineswith a hydrogen agent,

6. In a process-of making pungent com-v I 46 pounds treating guaiacol with a'c'ompound atom of the aromatic group ofguaiacol to form a substance readily separable from the ..'pungent j'product. in

of making pungent compounds, reacting guaiacol with a compound.

3. In a. process of the formula-RCONHCH OH wherein R is an alkyl. radicalcontainingfrom 6 to carbon atoms.

' 4. Ina process of making pungent compounds, condensing guaiacol with a compound of the formula RCONHCH OH wherein R is an alkyl'radical containingfrom 6 to 11 carbon atoms.

*5; In a'proc'ess of making pungent-coni- -pounds, treatin guaia'col with a compound a of the formula p v CONHCH OH wherein R is an alkyl radical containing from 6 to 11 carboniatoms and allowing the reaction to proceed-in the presence of a dehydrating of the formula RCONI-ICI-I OI-I wherein R n a processof making pungent comis an alkyl radical containing from 6 to 11 carbon atoms and allowingthe' reaction to proceed in the presencefof concentrated 11 E 7. In a process of making pungent compounds adding a dehydrating agent to an alcoholic solution of guaiacol and a compound of the formula RCONHCILOH wherein R is an alkyl radical containing from 6 to ll'carbon atoms and allowing the mixture to stand until the reaction is complete.

8. In a process of making pungent com pounds. adding concentrated H SO to an alcoholic solution of guaiacol and a compound of the formula RCONHCHOH wherein R is an alkyl radical containing 'from 6-to 11 carbon atoms and allowing the mixture to stand until the reaction is complete.

.9. Ina process ofmaking pungent compounds,' adding a dehydrating agent to an alcoholic solution of guaiacol and a compound of the formula RCONHCH OH wherein R- is an alkyl radical containing from 6 to 11 carbon atoms, allowing the mixture to stand until the reaction is complete and extracting the pungent material from the react on products bymeans of an organic solvent.-

10. In afprocess of making pungent .com

pounds adding adehydrating agent to an alcohollc' solution of guaiacol and a compound of the formula"RCONI-ICI-I OH wherein R is an 'alkyl 'radicalcontaining from 6 to 11 carbon atoms, allowing the mixture to stand until the reaction is complete and extracting the. pungent material from the reaction'products by meansof CI-ICl f DONALD B. BRADNER.

' MARY L. SHERRILL. I 

